EP0845973A4 - NAIL POLISH COMPOSITIONS - Google Patents

NAIL POLISH COMPOSITIONS

Info

Publication number
EP0845973A4
EP0845973A4 EP97925495A EP97925495A EP0845973A4 EP 0845973 A4 EP0845973 A4 EP 0845973A4 EP 97925495 A EP97925495 A EP 97925495A EP 97925495 A EP97925495 A EP 97925495A EP 0845973 A4 EP0845973 A4 EP 0845973A4
Authority
EP
European Patent Office
Prior art keywords
composition
straight
chain alkyl
branched chain
methyl
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
EP97925495A
Other languages
German (de)
English (en)
French (fr)
Other versions
EP0845973A1 (en
Inventor
Frank C Pagano
Anjali A Patil
Robert W Sandewicz
Waifong L Anton
Harry J Spinelli
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Revlon Consumer Products LLC
Original Assignee
Revlon Consumer Products LLC
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Revlon Consumer Products LLC filed Critical Revlon Consumer Products LLC
Publication of EP0845973A1 publication Critical patent/EP0845973A1/en
Publication of EP0845973A4 publication Critical patent/EP0845973A4/en
Withdrawn legal-status Critical Current

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Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q3/00—Manicure or pedicure preparations
    • A61Q3/02—Nail coatings
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/81—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
    • A61K8/8141—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
    • A61K8/8152—Homopolymers or copolymers of esters, e.g. (meth)acrylic acid esters; Compositions of derivatives of such polymers
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/80—Process related aspects concerning the preparation of the cosmetic composition or the storage or application thereof
    • A61K2800/88—Two- or multipart kits

Definitions

  • the invention is in the field of compositions for application to fingernails and toenails.
  • nitrocellulose is most commonly used as a film former in commercial nail enamels because it is inexpensive and readily available.
  • nail enamels containing cellulose-based film formers tend to provide good wear, adhesion, and gloss.
  • nitrocellulose has certain undesirable features. For example, it is essentially gun cotton, an explosive, so its manufacture and transport prior to incorporation into nail enamel poses certain hazards. Moreover, in some cases nitrocellulose may yellow in the nail enamel as it ages.
  • Nail enamels based upon polymeric film formers are known in the art. Some of these nail enamels do not contain nitrocellulose, or contain it in much smaller amounts. However, in many cases, the polymeric film formers do not provide the wear, adhesion, and gloss which is desired for commercial preparations. Thus, the goal for cosmetics companies is to develop nail enamels based upon polymeric systems (preferably without nitrocellulose, or containing reduced amounts of nitrocellulose) which provide superior gloss, adhesion, and wear when compared to the currently available products.
  • One object of the invention is to provide a polymer-based nail enamel composition which provides good wear, adhesion, and gloss.
  • Another object of the invention is to provide a polymer-based nail enamel composition which can be made either without cellulose-based film formers, or cont ⁇ ijiing significantly reduced levels of cellulose-based film formers.
  • Another object of the invention is to provide a method for forming a film on nails which is more resistant to wear when compared with normal methods and preparations.
  • Summary of the Invention The invention is directed to a nail enamel composition comprising, by weight of the total composition:
  • R,, R 3 , and R 5 are each independently H, a C,_ 30 straight or branched chain alkyl, aryl, aralkyl;
  • R 2 is a pyrrolidone, or a substituted or unsubstituted aromatic, alicyclic, or bicyclic ring where the substituents are C,. 30 straight or branched chain alkyl, or COOM wherein M is a C,. i0 straight or branched chain alkyl, pyrrolidone, or a substituted or unsubstituted aromatic, alicylic, or bicyclic ring where the substituents are C,. 30 straight or branched chain alkyl.
  • O
  • R 4 is -A-X-(OC — (CH 2 ) m -CCH 2 ) n — Z, or
  • the invention is also directed to a method for forming a film on a fingernail or toenail comprising: a) applying to said nail a composition comprising, by weight of the total composition:
  • R,, R 3 , and R 5 are each independently H, a C 1-30 straight or branched chain alkyl, aryl, aralkyl;
  • R 2 is a pyrrolidone, or a substituted or unsubstituted aromatic, alicyclic, or bicyclic ring where the substituents are C,. 30 straight or branched chain alkyl, or COOM wherein M is a C,. 30 straight or branched chain alkyl, pyrrolidone, or a substituted or unsubstituted aromatic, alicylic, or bicyclic ring where the substituents are
  • R4 is -A-X-(OC — (CH 2 ) m -CCH 2 ) n -Z, or
  • the invention is also directed to a kit comprised of two containers, container 1 and container 2, wherein container 1 contains a nail enamel composition comprised of:
  • R,, R 3 , and R 5 are each independently H, a C,. 30 straight or branched chain alkyl, aryl, aralkyl;
  • R 2 is a pyrrolidone, or a substituted or unsubstituted aromatic, alicyclic, or bicyclic ring where the substituents are C,. 30 straight or branched chain alkyl, or COOM wherein M is a C,. 30 straight or branched chain alkyl, pyrrolidone, or a substituted or unsubstituted aromatic, alicylic, or bicyclic ring where the substituents are C,. 3o straight or branched chain alkyl; O O R 4 i s -A-X-(OC — (CH 2 ) m -CCH 2 ) n -Z, or
  • the nail enamel compositions of the invention comprise 10-95 % by weight of the total composition, of solvent.
  • the solvent may be aqueous or non-aqueous or a mixture of both types of solvents.
  • Suitable non-aqueous solvents include aliphatic or aromatic ketones such as acetone, diacetone alcohol, dihydroxy acetone, ethyl butyl valerolactone, methyl ethyl ketone, and the like; aliphatic or aromatic alcohols such as methanol, propanol, benzyl alcohol, butoxyethanol, butoxypropanol, butyl alcohol, 3- methyl-3-methoxy-butanol, t-butyl alcohol, butylene glycol, diethylene glycol, abietyl alcohol, propylene carbonate, hexyl alcohol, isopropanol, and the like; glycol ethers; esters such as butyl acetate, ethyl acetate, etc.
  • the nail enamel compositions of the invention contain 5-90% by weight of the total composition of a copolymer resulting from the addition polymerization of monomer units A, B, and C wherein:
  • R,, R 3 , and R 5 are each independently H, a C,_ 30 straight or branched chain alkyl, aryl, aralkyl;
  • R 2 is a pyrrolidone, or a substituted or unsubstituted aromatic, alicyclic, or bicyclic ring where the substituents are C,. 30 straight or branched chain alkyl, or COOM wherein M is a C,. 30 straight or branched chain alkyl, pyrrolidone, or a substituted or unsubstituted aromatic, alicylic, or bicyclic ring where the substituents are C,. 30 straight or branched chain alkyl; O O
  • R 4 is -A-X-(OC » — (CH 2 ) m -C ⁇ CH 2 ) n — Z, or
  • the copolymers used in the compositions of the invention must be comprised of at least one A, one B, and one C monomer unit.
  • the copolymer may contain only one type of A monomer unit, or the A monomer component may comprise a combination of two or more different A monomer units.
  • the A component may comprise only methyl methacrylate, or it may comprise a combination of two or more monomer units such as methyl methacrylate, ethyl methacrylate, butyl methacrylate, and so on.
  • the final copolymer may contain only one type of B monomer, or it may contain a combination of two or more different types of B monomer units.
  • the final copolymer may contain only one type of C monomer unit, or it may contain a combination of two or more different types of C monomer units.
  • the copolymer may also contain other types of monomer units in addition to A, B, and C, so long as at least the A, B, and C monomer units are present.
  • Each unit provides a certain functional characteristic of the polymer, and it has been discovered that if the copolymer does not contain one or more of the units, the final nail enamel composition does not provide optimal wear.
  • the A monomer component of the copolymer is believed to provide the film forming characteristics desired in a nail enamel formulation.
  • the B monomer component is believed to provide an enhanced ability of the nail enamel composition to bind to the keratin of the nail.
  • the C monomer component of the copolymer may assist in providing proper adhesion to the nail. It is preferred that the copolymer contains 30-95% of the A monomer units,
  • the copolymers of the invention preferably have a number average molecular weight ranging from 20,000 to 100,000, preferably 27,000 to 53,000, and a weight average molecular weight ranging from 40,000 to 3,000,000, preferably 62,000 to 200,000, and glass transition temperature of 0-50°C , preferably 5-35°C.
  • R is hydrogen or a C,. 30 , preferably a C,. 8 alkyl
  • R 2 is a pyrrolidone, or a substituted or unsubstituted aromatic, alicyclic, or bicyclic ring where the substituents are C,. 30 straight or branched chain alkyl, or
  • R 15 unsubstituted aromatic ring are styrene and 2-methyl styrene.
  • An example of an A monomer unit where R 2 is a substituted aromatic ring is vinyl toluene.
  • R 2 in the A monomer unit is COOM where M is a straight or branched chain alkyl, pyrrolidone, or a substituted or unsubstituted aromatic, alicyclic, or bicyclic ring where the substituents are C,. 30 straight or branched chain alkyl.
  • An example of an A monomer unit where R 2 is COOM and M is an alicyclic ring is cyclohexyl methacrylate.
  • R 2 is COOM where M is a C,. 8 , preferably a C M alkyl.
  • the A monomer units comprise a combination of two to three different types of A monomer units wherein R, is hydrogen or methyl and R 2 is COOM where M is a C M alkyl, for example a combination of methyl methacrylate and butyl 30 methacrylate, a combination of methyl methacrylate, butyl acrylate, and butyl methacrylate, a combination of butyl acrylate and butyl methacrylate, and so on.
  • Examples of copolymers containing such combinations of A monomer units include:
  • the copolymer comprises only one type of A monomer unit as defined herein wherein R, is hydrogen or methyl, preferably methyl, and R 2 is COOM where M is a Cj_ 4 alkyl, preferably butyl, e.g. a copolymer consisting of about 70% butyl methacrylate, 20% acetoacetoxyethyl methacrylate, and 10% acrylic acid.
  • R 3 is hydrogen or a C,_ 8 alkyl, preferably methyl, and R, is
  • the B monomer unit comprises acetoacetoxyethyl methacrylate.
  • R 5 is hydrogen or a C,. 10 alkyl. More preferably, R s is hydrogen or methyl.
  • the copolymers used in the nail enamel compositions of the invention can be prepared by conventional polymerization techniques in which the monomers, solvent, and polymerization initiator are charged over a 1-24 hour period of time, preferably 2-8 hours, into a conventional polymerization reactor in which the constituents are heated to about 60-175 °C, preferably 80-100°C.
  • the polymer formed is a linear random polymer that has a weight average molecular weight of about 40,000 to 200,000 and a glass transition temperature of about 0-50°C.
  • the polymers may also be made by emulsion polymerization or suspension polymerization using conventional techniques.
  • Tg is the glass transition temperature of the polymer in degrees Kelvin
  • W,, W 2 , W 3 ...W n are the weight fractions of each of the components of the polymer and Tg ! ,.
  • Tg 2 , Tg 3 , Tg n are the Tg, in degrees Kelvin, ( ne homopolymer made from the individual components of the polymer.
  • Typical polymerization initiators that are used in the process are as follows: azo type initiators such as azo-bis-isobutyronitrile, l,l'azo-bis(cyanocyclohexane), peroxy acetates such as t-butyl peracetate, peroxides such as di- t-butyl peroxide, benzoates such as t-butyl perbenzoates, octoates such as t-butyl peroctoate and the like.
  • azo type initiators such as azo-bis-isobutyronitrile, l,l'azo-bis(cyanocyclohexane)
  • peroxy acetates such as t-butyl peracetate
  • peroxides such as di- t-butyl peroxide
  • benzoates such as t-butyl perbenzoates
  • octoates such as t-butyl peroctoate and the like.
  • Typical solvents that can be used are ketones such as methyl amyl ketone, methyl isobutyl ketone, methyl ethyl ketone, aromatic hydrocarbons such as toluene, and xylene, alkylene carbonates such as propylene carbonate, n-methyl pyrrolidone, ethers, esters, acetate and mixtures of any of the above.
  • An aqueous composition can be formed from the acrylic polymer prepared by solution polymerization by stripping off the solvent and adding ammonia or amine and water preferably with some organic solvent to form an aqueous dispersion, hydrosol, or solution.
  • An alternate method of forming an aqueous composition is to disperse the polymer into water or water/solvent mixtures with the aid of surfactants.
  • Higher molecular weight acrylic polymers can be formed by conventional emulsion polymerization techniques by emulsifying a mixture of monomer, water, surfactant, and polymerization catalyst and charging the resulting emulsion into a conventional polymerization reactor and heating the constituents in the reactor to about 60-95 °C. for about 15 minutes to about 8 hours.
  • the resulting latex typically has a polymer solids content of about 10-40% of polymer dispersed in aqueous medium and the polymer has a weight average molecular weight of about 200,000 to 3,000,000.
  • Typical catalysts used in the emulsion polymerization process are ammonium persulfate, hydrogen peroxide, sodium meta bisulfite, sodium sulfoxylate, and the like.
  • Typical surfactants that may be used in the emulsion polymerization process are nonylphenoxypolyethyleneoxy ethanol sulfate, allyl dodecyl sulfosuccinate, alkyl phenoxy polyethylene oxy ethanol, sodium lauryl sulfate, and mixtures thereof.
  • the acrylic polymer in an aqueous carrier may be neutralized with ammonia, typically ammonium hydroxide or an amine and the pH is adjusted to about 7 to 10.
  • Useful amines are alkyl amines such as ethylamine, tertiary amines such as trimethylamine, triethylamine, dimethylaniline, diethylaniline, triphenylamine, dimethylethanol amine, triethanol amine, and the like.
  • the nail enamel compositions of the invention may be pigmented or clear. If pigmented, generally 0.01-30% by weight of the total composition, preferably 0.5-20%, more preferably 1-15% of pigment is suggested. Pigments suitable for use in nail enamel compositions are well known and include iron oxides, D&C and FD&C colors, titanium dioxide, and the like.
  • the pigments may be treated or coated with agents which modify the surface properties such as silicones. Examples of silicone treated pigments which can be used in the compositions of the invention are set forth in U.S. patent no. 4,832,944, which is hereby inco ⁇ orated by reference.
  • Suitable suspending agents are montmorillonite minerals and derivatives thereof, such as stearalkonium bentonite, hectorites, attapulgite, bentones, and the like, as well as polymeric compounds known as associative thickeners.
  • Suitable associative thickeners generally contain a hydrophilic backbone and hydrophobic side groups. Examples of such thickeners include polyacrylates with hydrophobic side groups, cellulose ethers with hydrophobic side groups, polyurethane thickeners.
  • hydrophobic side groups are long chain alkyl groups such as dodecyl, hexadecyl, or octadecyl; alkylaryl groups such as octylphenyl or nonyphenyl.
  • cellulosic film formers include nitrocellulose, cellulose acetate isobutyrate, cellulose acetate propionate, and the like. If cellulosic film formers are added, a level of 0.1-15%, preferably 0.5-7%, more preferably 0.5-5% by weight of the total composition is suggested.
  • the preferred embodiment of the invention is a nail enamel composition comprising: 10-95%, preferably 15-80%, more preferably 20-75% solvent,
  • Silicone glycol copolymers which may be used in the compositions of the invention are polymethylsiloxanes wherein a portion of the methylsiloxane units are substituted with polyalkylene glycol ether moieties.
  • silicone glycol copolymers having a viscosity ranging from 1.0 to 500,000, preferably 1.0 to 2,000 centipoise at 25°C, a specific gravity ranging from 0.80 to 1.030 at 25°C , and comprise approximately 80% dimethylsiloxane units and 20% propylene oxide substituted methyl siloxane units. Silicone glycol copolymers having this description are commercially available from a variety of sources including Dow Corning under the tradenames Dow Corning Additive 3, 7, 11, 14, 18, 21, 24, 26, 28, 29, 51, 54, 56, 57, and 1248.
  • compositions of the invention may also contain other ingredients such as emulsifiers, humectants, ancillary film formers, defoamers, plasticizers, preservatives, and the like.
  • the invention also comprises a method for forming a film on the fingernail or toenail by applying the compositions of the invention to the nail.
  • the composition applied to the nails is allowed to dry for an appropriate period of time ranging from 60 seconds to 60 minutes.
  • the resulting film exhibits improved wear. It may be desired to apply the composition of the invention to the nails, and then apply as a top coat, a composition which utilizes a cellulosic film former as the topcoat, or, in the alternative, to apply the cellulosic film former composition first to the nails and apply as a topcoat the composition of the invention.
  • the composition of the invention and the cellulosic-based composition can be layered in any manner desired.
  • the cellulose-based composition will generally comprise 1-80% of one or more of the solvents mentioned herein, 0.1-25% cellulose film former, and 0.1-40% plasticizer as a topcoat to said nails.
  • the cellulose film former is nitrocellulose and the plasticizer is a glyceryl, glycol, or citrate ester as disclosed and claimed in U.S. patent no. 5,225,185 which is hereby inco ⁇ orated by reference.
  • the invention also is directed to a kit for applying nail enamel to the nails, said kit comprising two containers, container 1 and container 2.
  • Container 1 contains the nail enamel composition of the invention
  • container 2 contains a cellulose-based nail enamel composition mentioned above.
  • one of the compositions is pigmented.
  • the consumer who purchases the kit applies layers of each composition in the desired order. The combination provides significantly improved wear.
  • the composition of the invention is pigmented
  • the cellulose-based composition is clear.
  • the consumer applies the cellulose based composition as a basecoat and topcoat, and the pigmented composition of the invention as the middle, color coat.
  • wear indicates the overall resistance of the dried nail enamel film to chipping, loss of gloss, scratching, or other reduction in aesthetics due to tackiness of the coating or sensitivity of the coating to heat and moisture when on the nails.
  • Cellulose acetate propionate 2.00 ⁇ Polymer a polymer solution of 70% butyl methacrylate, 20% acetoacetoxyethylmethacrylate, 10% acrylic acid (60% solids). The polymer had a number average molecular weight of 44,000 and a weight average molecular weight of 102,000, a polydispersity of 2.3, and a glass transition temperature of about 15° C.
  • compositions were made by combining the polymer, solvents, pigment, and other ingredients and mixing well.
  • Polymer 1 50% solution in a 50/50 mixture of ethyl acetate and butyl acetate of a polymer comprised of 10% methyl methacrylate, 60% butyl methacrylate, 20% acetoacetoxyethyl methacrylate, and 10% acrylic acid.
  • Polymer 2 51 % solution in a 50/50 mixture of ethyl acetate and butyl acetate of a polymer comprised of 10% methyl methacrylate, 5% butyl acrylate, 55% butyl methacrylate, 20% acetoacetoxyethyl methacrylate, and 10% acrylic acid.
  • the polymer had a weight average molecular weight of 176,000, a number average molecular weight of 49,200, a polydispersity of 3.6 and a glass transition temperature of 16°C.
  • Polymer 3 50% solution in a 50/50 mixture of ethyl acetate and butyl acetate of a polymer comprised of 5% butyl acrylate, 65% butyl methacrylate, 20% acetoacetoxyethyl methacrylate, and 10% acrylic acid.
  • the polymer had a weight average molecular weight of 187,000, a number average molecular weight of 55,000, and a glass transition temperature of 10°C.
  • Pigmented nail enamel compositions were made as follows:
  • Nitrocellulose base * the formula for Nitrocellulose base is as follows:
  • Formulas 3-2 and 3-4 of Example 3 were subjected to blind studies to ascertain he differences in performance characteristics. Test subjects applied Formula 3-2 to each 1 .0 __ of five nails and Formula 3-4 to the other five nails. Wear was evaluated by J a test moderator on a scale of 1 to 10 with 10 being the best and 1 being the worst. The results after averaging are as follows:
  • Formulas 3-3 and 3-4 of Example 3 were subjected to blind studies to ascertain differences in wear characteristics. Test subjects applied Formula 3-3 to each of five nails, and Formula 3-4 to the other five nails. Wear was evaluated by a test moderator on a 1 to 10 scale, with 10 being the best and 1 being the worst. The results after
  • Formula 3-3 containing an acrylate copolymer as called for by the invention, exhibits improved wear when compared with Formula 3-4 which is a nail enamel formulation not containing an acrylate copolymer as called for by the invention.
  • Polymer 1 - contains 40% methylmethacrylate, 30% butylmethacrylate, 20% acetoacetoxyethylmethacrylate, and 10% acrylic acid as 50.3% solids in a solvent comprised of 80% ethyl acetate and 20% butyl acetate.
  • Polymer 2 - contains 30% methylmethacrylate, 40% butylmethacrylate, 20% acetoacetoxyethylmethacrylate, and 10% acrylic acid as 50.4% solids in a solvent comprised of 80% ethyl acetate and 20% butyl acetate.
  • the polymer had a weight average molecular weight of 93,000 and a number average molecular weight of 41,000, a polydispersity of 2.3 and a glass transition temperature of 35 °C.
  • Polymer 3 - contains 70% ethylmethacrylate, 20% acetoacetoxyethylmethacrylate, and 10% acrylic acid as 50% solids in a solvent comprised of 80% ethyl acetate and 20% butyl acetate.
  • Pigmented nail enamel compositions were made as follows:
  • Formula 6-4 was applied to alternate clean nails of 6 panelists and Formula 7 was applied to the other alternate nails so that each product was applied to 5 total nails per panelist. Immediately following application, panelists evaluated
  • Formula 6-6 was applied to alternate clean nails of 6 panelists and Formula 7 was applied to the other alternate nails so that each product was applied to 5 total nails per panelist. Immediately following application, panelists evaluated
  • a nail enamel formula was made as follows: w/w%
  • Polymer 1 contained 70% butylmethacrylate, 20% acetoacetoxyethyl methacrylate, and 10% acrylic acid neutralized with ammonium hydroxide. The copolymer was dissolved, the solution containing 30% water, 20% isopropyl alcohol, and 10% methoxypropanol.
  • Nail enamel compositions were made as follows: w/w%
  • Titanium dioxide 0.25 0.25 0.25 0.25 0.25
  • Polymer 1 comprises 80% butyl methacrylate, 20% acetoacetoxyethylmethacrylate. the polymer had a weight average molecular weight of 47,900, a number average molecular weight of 25,100, a polydispersity of 1.91 and a glass transition temperature of 8°C.
  • Polymer 2 comprises 70% butyl methacrylate, 20% acetoacetoxyethylmethacrylate, and 10% acrylic acid.
  • Polymer 3 comprises 80% butyl methacrylate, 10% acetoacetoxyethylmethacrylate, and 10% acrylic acid.
  • Formula 9-1 6/6 4 panelists preferred application of Formula 9-4.
  • Formula 9-4 6/6 4 panelists said Formula 9-1 was stringy and difficult to apply.
  • Formula 9-1 6/6 2 panelists preferred Formula 9-4 for appearance, Formula 9-4 6/6 other 4 panelists had no preference
  • Ethyl acetate 117 grams; n-butyl methacrylate, 35 grams; 2-acetoacetoxyethyl methacrylate, 10 grams; and acrylic acid, 5 grams; were charged into the reactor. The contents of the reactor were brought to its reflux temperature. A solution of 2,2 - azobis(2,4-dimethylvaleronitrile), 0.25 grams in ethyl acetate, 5 grams; was injected into the reactor. Feed 1 (n-butyl methacrylate), 140 grams; 2-acetoacetoxyethyl methacrylate, 40 grams; and acrylic acid, 20 grams; was then started and added to the reactor over 60 minutes.
  • Feed 2 (2,2 -azobis(2,4-diemthylvaleronitrile), 1.0 gram in ethyl acetate, 20 grams) was started at the end of Feed 1 and added to the reactor over the next 340 minutes. The mixture was held at its reflux temperature for another 30 minutes, then allowed to cool to room temperature.
  • the resultant polymer had a Tg (glass transition temperature) of about 15°C, a weight average molecular weight of 102,000 and number average molecular weight of 44,000 and polydispersity of 2.3. This polymer was used in formulating the nail enamel compositions of Example 1.
  • EXAMPLE 11 An aqueous-based nail enamel composition was prepared as follows: w/w% Polymer Solution* 75.00
  • the Polymer Solution contains 40% w/w Polymer and 60% w/w of a solution comprised (by weight of the total solution) of 30% water, 20% isopropyl alcohol, and 10% methoxypropanol.
  • Example 11 The nail enamel composition of this Example 11 was tested for wear in a double blind study using the Nitrocellulose base of Example 3 as the control.
  • the Example 11 nail enamel was applied to alternate nails of six panelists, and the Nitrocellulose base to the remaining alternate nails of the six panelists. Wear was evaluated by a test moderator every day for four days, by grading on a 1 to 10 scale with 10 being the best and 1 being the worst. The wear results, after averaging, are set forth below:
  • the Polymer is comprised of 70% butyl methacrylate, 20% acetoacetoxy ethylmethacrylate, and 10% acrylic acid.
  • the Polymer solution is an anionic acrylic emulsion where the Polymer is present at a concentration of 34%.

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Birds (AREA)
  • Epidemiology (AREA)
  • Cosmetics (AREA)
EP97925495A 1996-05-10 1997-05-09 NAIL POLISH COMPOSITIONS Withdrawn EP0845973A4 (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US646676 1996-05-10
US08/646,676 US5772988A (en) 1996-05-10 1996-05-10 Nail enamel compositions from acetoacetoxy methacrylate copolymer
PCT/US1997/007858 WO1997042930A1 (en) 1996-05-10 1997-05-09 Nail enamel compositions

Publications (2)

Publication Number Publication Date
EP0845973A1 EP0845973A1 (en) 1998-06-10
EP0845973A4 true EP0845973A4 (en) 1999-05-06

Family

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Family Applications (1)

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EP97925495A Withdrawn EP0845973A4 (en) 1996-05-10 1997-05-09 NAIL POLISH COMPOSITIONS

Country Status (7)

Country Link
US (1) US5772988A (ja)
EP (1) EP0845973A4 (ja)
JP (1) JPH11509869A (ja)
AU (1) AU707799B2 (ja)
CA (1) CA2226567A1 (ja)
WO (1) WO1997042930A1 (ja)
ZA (1) ZA974081B (ja)

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US6818207B1 (en) * 1998-03-09 2004-11-16 Creative Nail Design, Inc. Artificial nail compositions and related method
US6197316B1 (en) * 1998-05-01 2001-03-06 The Procter & Gamble Company Nail polish kits
US5965111A (en) * 1998-05-01 1999-10-12 The Procter & Gamble Company Fast drying water-borne nail polish
US6123931A (en) * 1998-05-01 2000-09-26 The Procter & Gamble Company Polyurethane and polyacryl nail polish compositions
US6080413A (en) * 1998-05-01 2000-06-27 The Procter & Gamble Company Polyurethane nail polish compositions
US6136300A (en) * 1998-05-01 2000-10-24 The Procter & Gamble Company Long wear nail polish having adhesion, toughness, and hardness
US6306375B1 (en) 1998-05-01 2001-10-23 The Procter & Gamble Company Long wear nail polish having defined surface properties
US6080414A (en) * 1998-05-01 2000-06-27 The Proctor & Gamble Company Long wear nail polish
FR2786376B1 (fr) 1998-11-27 2001-10-26 Oreal Pinceau de vernis a ongles et ensemble d'application de vernis a ongles muni d'un tel pinceau
US20020018759A1 (en) * 2000-05-04 2002-02-14 Pagano Frank Charles Nail enamel compositions, related methods, and a two component kit for painting the nails
US20040151680A1 (en) * 2003-02-05 2004-08-05 Patil Anjali Abhimanyu Cosmetic compositions containing phenyl silicones
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EP0845973A1 (en) 1998-06-10
ZA974081B (en) 1997-12-09
AU707799B2 (en) 1999-07-22
CA2226567A1 (en) 1997-11-20
JPH11509869A (ja) 1999-08-31
WO1997042930A1 (en) 1997-11-20
AU3062097A (en) 1997-12-05

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